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How to get fromLong Island to Winchesterby plane, car ferry, train, bus (Flixbus), car, subway, or train (Amtrak)

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There are 8 ways to get from Long Island to Winchester by plane, car ferry, train, bus (Flixbus), car, subway, or train (Amtrak)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly from John F. Kennedy International Airport

    best
    1. Fly from John F. Kennedy International Airport (JFK) to Boston Logan Airport (BOS)plane plane JFK - BOS
    2h 47m
    $215–1,016

  2. Bus (Flixbus)

    cheapest
    1. Take the bus from Queens Jamaica to Bostonbus bus FlixBus 2612
    7h 2m
    $37–75

  3. Car ferry, train

    1. Take the carferry from Orient Point to New Londoncarferry car ferry New London
    2. Take the train from New London to Bostontrain train Northeast Regional
    5h 14m
    $55–164

  4. Drive 215.7 mi

    1. Drive from Brooklyn to Winchestercar car 215.7 mi
    4h 12m
    $40–57

  5. Fly from Laguardia Airport

    1. Fly from Laguardia Airport (LGA) to Boston Logan Airport (BOS)plane plane LGA - BOS
    2h 53m
    $59–354

  6. Fly from Long Island Mac Arthur Airport

    1. Fly from Long Island Mac Arthur Airport (ISP) to Boston Logan Airport (BOS)plane plane ISP - BOS
    3h 8m
    $261–359

  7. Subway, train to Newark Liberty International Airport, fly

    1. Take the subway from Roosevelt Island to 34 St-Herald Sqsubway subway
    2. Take the train from New York Penn Station to Newark Airport Railroad Stationtrain train
    3. Fly from Newark Liberty International Airport (EWR) to Boston Logan Airport (BOS)plane plane EWR - BOS
    4h 56m
    $493–1,647

  8. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Bostontrain train Acela
    5h 43m
    $77–173

Long Island to Winchester by bus, foot, and subway (Flixbus)

Calendar58Weekly Services
Duration7h 2mAverage Duration
Ticket$37Cheapest Price
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Questions & Answers

Map of how to get from Long Island to Winchester.ExpandLaunch map view
  • Distance: 205.8 mi
  • Duration: 2h 47m

What companies run services between Long Island, Suffolk County, NY, USA and Winchester, MA, USA?

American Airlines, JetBlue Airways, and Delta fly from John F. Kennedy International Airport (JFK) to Boston Logan Airport (BOS) hourly. Alternatively, Flixbus USA operates a bus from Queens Jamaica to Boston every 4 hours. Tickets cost $30–60 and the journey takes 4h 40m.

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